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The gas‐phase ozonolysis reaction of methylbutenol: A mechanistic study
Author(s) -
Almatarneh Mansour H.,
Elayan Ismael A.,
AbuSaleh Abd AlAziz A.,
Altarawneh Mohammednoor,
Ariya Parisa A.
Publication year - 2019
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.25888
Subject(s) - chemistry , ozonolysis , ozonide , formaldehyde , radical , dissociation (chemistry) , photochemistry , epoxide , reactivity (psychology) , formic acid , reaction mechanism , acetone , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The gas‐phase ozonolysis reaction of methylbutenol through the Criegee mechanism is investigated. The initial reaction leads to a primary ozonide (POZ) formation with barriers in the range of 10–28 kJ mol −1 . The formation of 2‐hydroxy‐2‐methyl‐propanal (HMP) and formaldehyde‐oxide is more favorable, by 10 kJ mol −1 , than the syn ‐CI and formaldehyde. The unimolecular dissociation of the more stable syn ‐CI via 1,5‐H transfer into an epoxide is more favored than the epoxide and 3 O 2 formation. The ester channel led to the formation of the acetone and formic acid favorably from the anti ‐CI. The hydration of the anti ‐CI with H 2 O and (H 2 O) 2 is significantly barrierless with a higher plausibility to the latter, and thus they may lead to the formation of peroxides and ultimately OH radicals, as well as airborne particulate matter. Reaction of anti ‐CI with water dimers enhances its atmospheric reactivity by a factor of 28 in reference to water monomers.